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Search results; Over 1,000 homes in Madison

Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 private bathroom
25–30 Aug
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4.98 out of 5 average rating, 227 reviews
Top guest favourite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
6 bedrooms, 11 beds, 4.5 bathrooms
5–10 Sept
4.99 out of 5 average rating, 142 reviews
Top guest favourite
Flat in Church Creek
Nature's Rest in Church Creek
1 bedroom, 1 queen bed, 1 bathroom
10–15 Aug
4.97 out of 5 average rating, 450 reviews
Guest favourite
Home in Woolford
Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba
7 bedrooms, 13 beds, 5 bathrooms
29 Aug – 3 Sept
4.98 out of 5 average rating, 87 reviews
Top guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 101 reviews
Top guest favourite
Room in Cambridge
Farm View Room at Happy Campers
2 single beds, 1 bathroom
17–22 Aug
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Room in Cambridge
Sailor's Retreat Captain's Quarters
1 king bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 96 reviews
Guest favourite
Room in Cambridge
Choptank Charm - 1 bed option
1 king bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 8 reviews
Featured hotel
Room in St. Michaels
Standard queen room
1 queen bed, 1 bathroom
2–7 Aug
New place to stay
Top guest favourite
Home in Madison
Bayfront Gem w/ Amazing Water Views + Pond!
4 bedrooms, 7 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 59 reviews
Top guest favourite
Home in Woolford
Waterfront Getaway with Dock
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.94 out of 5 average rating, 188 reviews
Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
4 bedrooms, 7 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Houseboat in Solomons
Good Vibe Villa, Tiny houseboat
1 queen bed, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 197 reviews
Home in Cambridge
Amazing Everything!
4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 247 reviews
Top guest favourite
Home in Cambridge
Chesapeake Sunset Cottage
2 bedrooms, 2 queen beds, 2 bathrooms
31 Aug – 5 Sept
4.97 out of 5 average rating, 106 reviews
Guest favourite
Home in Cambridge
Outline
3 bedrooms, 6 beds, 2 bathrooms
31 Aug – 5 Sept
4.91 out of 5 average rating, 33 reviews
Guest favourite
Room in Cambridge
Stevens’ Gift, Grandfather’s room
1 double bed, 2 bathrooms
1–6 Aug
4.94 out of 5 average rating, 50 reviews
Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct